Ammonia → Phenylmethyl N-[2-(aminosulfonyl)ethyl]carbamate

HRID 1405941Notes

Reaction equation

HRID 1405941 reaction equation
[NH3:1].O1CCOCC1.[CH2:8]([O:15][C:16]([NH:18][CH2:19][CH2:20][S:21](Cl)(=[O:23])=[O:22])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(#N)C>[CH2:8]([O:15][C:16]([NH:18][CH2:19][CH2:20][S:21]([NH2:1])(=[O:23])=[O:22])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 13255033Benzyl [2-(chlorosulfonyl)ethyl]carbamate

Product 1

HCID 11615848Phenylmethyl N-[2-(aminosulfonyl)ethyl]carbamateYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a reaction flask, 100 ml of aqueous ammonia and 100 ml of dioxane were added, and a solution of 17.9 g 2-benzyloxyformamidoethylsulfonyl chloride in acetonitrile (30 ml) was added dropwise under ice-bath condition. The mixture was stirred for 2 h at room temperature. Upon the end of the dropping, the mixture was concentrated under a reduced pressure, and was then filtered, the filter cake was washed with water, and dried to obtain 12.3 g of white solid, yield 74%.

Workup

  1. concentrationUpon the end of the dropping, the mixture was concentrated under a reduced pressure
  2. filtrationwas then filtered
  3. washthe filter cake was washed with water
  4. customdried

Sources & evidence

ORD record
ord-2e84be28666b4e1282446e0f9bb9ae8f
Source dataset
uspto-grants-2014_12
Patent number
US08916574B2

Reaction notes

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